#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:14:52 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281431 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/60/7246095.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7246095
loop_
_publ_author_name
'Rekha Rout, Smruti'
'Kenguva, Gowtham'
'Giri, Lopamudra'
'Dandela, Rambabu'
_publ_section_title
;
 Novel salts of the antiemetic drug domperidone: synthesis,
 characterization and physicochemical property investigation
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              513
_journal_page_last               524
_journal_paper_doi               10.1039/D2CE00902A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C22 H25 Cl N5 O2,C2 O4'
_chemical_formula_sum            'C24 H25 Cl N5 O6'
_chemical_formula_weight         514.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-30 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.04(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.917(1)
_cell_length_b                   10.099(1)
_cell_length_c                   16.199(1)
_cell_measurement_reflns_used    3692
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.963
_cell_measurement_theta_min      0.946
_cell_volume                     2377.4(3)
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture photon 100 CMOS detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23969
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_min         2.394
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       block
_exptl_crystal_F_000             1076.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.6346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3692
_reflns_number_total             4882
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00902a2.cif
_cod_data_source_block           DomOxa_1_0m_a_a
_cod_depositor_comments
'Adding full bibliography for 7246090--7246098.cif.'
_cod_original_cell_volume        2377.3(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C24 H25 Cl N5 O6 '
_cod_database_code               7246095
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.61452(5) 0.36404(7) -0.00689(4) 0.0695(2) Uani 1 1 d . . . . .
O3 O 0.63435(10) 0.23829(16) 0.43408(9) 0.0467(4) Uani 1 1 d . . . . .
O2 O 0.99852(10) 0.56941(16) 0.34357(10) 0.0493(4) Uani 1 1 d . . . . .
N3 N 0.79469(11) 0.31182(16) 0.54887(10) 0.0330(4) Uani 1 1 d . . . . .
O4 O 0.58183(11) 0.40373(17) 0.50091(10) 0.0549(4) Uani 1 1 d . . . . .
O1 O 0.61921(12) -0.02266(18) 0.56416(11) 0.0594(5) Uani 1 1 d . . . . .
N4 N 0.86293(11) 0.44895(17) 0.32218(10) 0.0370(4) Uani 1 1 d . . . . .
N5 N 0.89903(12) 0.54301(17) 0.21158(11) 0.0376(4) Uani 1 1 d . . . . .
O5 O 0.41773(12) 0.3963(2) 0.39148(12) 0.0672(5) Uani 1 1 d . . . . .
O6 O 0.46628(13) 0.2338(2) 0.32247(12) 0.0707(6) Uani 1 1 d . . . . .
N2 N 0.63203(13) 0.12597(19) 0.67561(12) 0.0458(4) Uani 1 1 d . . . . .
N1 N 0.50157(15) 0.1208(2) 0.58002(14) 0.0501(5) Uani 1 1 d . . . . .
C17 C 0.81645(13) 0.47915(18) 0.18245(12) 0.0347(4) Uani 1 1 d . . . . .
C11 C 0.87326(13) 0.2462(2) 0.52196(12) 0.0357(4) Uani 1 1 d . . . . .
H11A H 0.871487 0.151610 0.531939 0.043 Uiso 1 1 calc R U . . .
H11B H 0.930941 0.280301 0.555301 0.043 Uiso 1 1 calc R U . . .
C22 C 0.79260(13) 0.41886(19) 0.25257(12) 0.0345(4) Uani 1 1 d . . . . .
C16 C 0.92824(14) 0.5255(2) 0.29684(13) 0.0371(4) Uani 1 1 d . . . . .
C13 C 0.86833(14) 0.4199(2) 0.41156(12) 0.0372(4) Uani 1 1 d . . . . .
H13 H 0.927276 0.454690 0.443672 0.045 Uiso 1 1 calc R U . . .
C18 C 0.76332(15) 0.4641(2) 0.10168(13) 0.0405(5) Uani 1 1 d . . . . .
H18 H 0.779849 0.501875 0.054909 0.049 Uiso 1 1 calc R U . . .
C1 C 0.57410(15) 0.2191(2) 0.69971(13) 0.0430(5) Uani 1 1 d . . . . .
C23 C 0.57405(14) 0.3190(2) 0.44470(13) 0.0384(5) Uani 1 1 d . . . . .
C15 C 0.79780(15) 0.45930(19) 0.53592(13) 0.0380(4) Uani 1 1 d . . . . .
H15A H 0.854437 0.494764 0.570396 0.046 Uiso 1 1 calc R U . . .
H15B H 0.746621 0.500822 0.553703 0.046 Uiso 1 1 calc R U . . .
C12 C 0.86787(15) 0.2716(2) 0.42863(12) 0.0380(4) Uani 1 1 d . . . . .
H12A H 0.811986 0.232655 0.395048 0.046 Uiso 1 1 calc R U . . .
H12B H 0.919910 0.230369 0.412160 0.046 Uiso 1 1 calc R U . . .
C10 C 0.79061(15) 0.2823(2) 0.63851(12) 0.0391(5) Uani 1 1 d . . . . .
H10A H 0.735097 0.321125 0.649744 0.047 Uiso 1 1 calc R U . . .
H10B H 0.842820 0.323596 0.676360 0.047 Uiso 1 1 calc R U . . .
C14 C 0.79264(15) 0.4906(2) 0.44367(13) 0.0397(5) Uani 1 1 d . . . . .
H14A H 0.798505 0.585445 0.436951 0.048 Uiso 1 1 calc R U . . .
H14B H 0.733110 0.463613 0.410068 0.048 Uiso 1 1 calc R U . . .
C9 C 0.79132(15) 0.1349(2) 0.65767(14) 0.0430(5) Uani 1 1 d . . . . .
H9A H 0.853531 0.108043 0.684432 0.052 Uiso 1 1 calc R U . . .
H9B H 0.772797 0.086404 0.604879 0.052 Uiso 1 1 calc R U . . .
C19 C 0.68384(16) 0.3896(2) 0.09389(13) 0.0429(5) Uani 1 1 d . . . . .
C6 C 0.49159(16) 0.2163(2) 0.63845(14) 0.0444(5) Uani 1 1 d . . . . .
C21 C 0.71265(14) 0.3453(2) 0.24317(13) 0.0398(5) Uani 1 1 d . . . . .
H21 H 0.696332 0.306175 0.289638 0.048 Uiso 1 1 calc R U . . .
C2 C 0.58520(17) 0.3029(2) 0.76834(15) 0.0505(6) Uani 1 1 d . . . . .
H2 H 0.639977 0.304962 0.809390 0.061 Uiso 1 1 calc R U . . .
C7 C 0.58655(17) 0.0649(2) 0.60172(15) 0.0482(5) Uani 1 1 d . . . . .
C20 C 0.65750(15) 0.3318(2) 0.16209(14) 0.0436(5) Uani 1 1 d . . . . .
H20 H 0.602926 0.283947 0.153737 0.052 Uiso 1 1 calc R U . . .
C24 C 0.48107(15) 0.3112(2) 0.38007(15) 0.0475(5) Uani 1 1 d . . . . .
C8 C 0.72748(16) 0.0987(3) 0.71533(14) 0.0498(6) Uani 1 1 d . . . . .
H8A H 0.734367 0.005366 0.729424 0.060 Uiso 1 1 calc R U . . .
H8B H 0.744825 0.148795 0.767606 0.060 Uiso 1 1 calc R U . . .
C5 C 0.41927(17) 0.2972(2) 0.64363(16) 0.0523(6) Uani 1 1 d . . . . .
H5A H 0.364768 0.296131 0.602213 0.063 Uiso 1 1 calc R U . . .
C3 C 0.51193(19) 0.3839(2) 0.77410(16) 0.0543(6) Uani 1 1 d . . . . .
H3 H 0.517614 0.441380 0.819843 0.065 Uiso 1 1 calc R U . . .
C4 C 0.43070(19) 0.3808(2) 0.71322(17) 0.0569(6) Uani 1 1 d . . . . .
H4 H 0.382547 0.436004 0.718923 0.068 Uiso 1 1 calc R U . . .
H111 H 0.4649(19) 0.098(3) 0.5401(18) 0.052(8) Uiso 1 1 d . . . . .
H112 H 0.7411(17) 0.280(2) 0.5146(15) 0.044(6) Uiso 1 1 d . . . . .
H113 H 0.924(2) 0.600(3) 0.1799(18) 0.068(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N3 C10 113.63(15) . . ?
C11 N3 C15 110.31(15) . . ?
C10 N3 C15 109.96(15) . . ?
C16 N4 C22 109.65(16) . . ?
C16 N4 C13 121.56(16) . . ?
C22 N4 C13 128.52(16) . . ?
C16 N5 C17 110.09(17) . . ?
C7 N2 C1 109.28(19) . . ?
C7 N2 C8 122.75(19) . . ?
C1 N2 C8 127.84(19) . . ?
C7 N1 C6 110.5(2) . . ?
N5 C17 C18 131.03(18) . . ?
N5 C17 C22 107.26(17) . . ?
C18 C17 C22 121.64(18) . . ?
N3 C11 C12 110.29(15) . . ?
C21 C22 N4 132.90(18) . . ?
C21 C22 C17 120.89(18) . . ?
N4 C22 C17 106.20(17) . . ?
O2 C16 N5 127.64(19) . . ?
O2 C16 N4 125.55(19) . . ?
N5 C16 N4 106.80(17) . . ?
N4 C13 C14 111.41(17) . . ?
N4 C13 C12 112.06(16) . . ?
C14 C13 C12 111.39(17) . . ?
C17 C18 C19 116.34(19) . . ?
C2 C1 N2 132.3(2) . . ?
C2 C1 C6 120.8(2) . . ?
N2 C1 C6 106.92(19) . . ?
O4 C23 O3 126.9(2) . . ?
O4 C23 C24 117.18(18) . . ?
O3 C23 C24 115.94(18) . . ?
N3 C15 C14 110.37(16) . . ?
C11 C12 C13 110.24(16) . . ?
N3 C10 C9 113.16(16) . . ?
C15 C14 C13 111.29(17) . . ?
C10 C9 C8 112.59(19) . . ?
C20 C19 C18 123.23(19) . . ?
C20 C19 Cl1 118.07(17) . . ?
C18 C19 Cl1 118.69(17) . . ?
C5 C6 N1 131.7(2) . . ?
C5 C6 C1 121.6(2) . . ?
N1 C6 C1 106.6(2) . . ?
C22 C21 C20 117.91(19) . . ?
C1 C2 C3 117.7(2) . . ?
O1 C7 N1 128.2(2) . . ?
O1 C7 N2 125.2(2) . . ?
N1 C7 N2 106.6(2) . . ?
C19 C20 C21 120.0(2) . . ?
O6 C24 O5 121.4(2) . . ?
O6 C24 C23 122.8(2) . . ?
O5 C24 C23 115.76(19) . . ?
N2 C8 C9 111.71(18) . . ?
C6 C5 C4 117.3(2) . . ?
C4 C3 C2 121.2(2) . . ?
C3 C4 C5 121.4(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C19 1.743(2) . ?
O3 C23 1.254(2) . ?
O2 C16 1.229(2) . ?
N3 C11 1.495(2) . ?
N3 C10 1.497(2) . ?
N3 C15 1.506(3) . ?
O4 C23 1.236(3) . ?
O1 C7 1.235(3) . ?
N4 C16 1.377(3) . ?
N4 C22 1.389(3) . ?
N4 C13 1.462(2) . ?
N5 C16 1.363(3) . ?
N5 C17 1.376(3) . ?
O5 C24 1.321(3) . ?
O6 C24 1.199(3) . ?
N2 C7 1.381(3) . ?
N2 C1 1.391(3) . ?
N2 C8 1.450(3) . ?
N1 C7 1.359(3) . ?
N1 C6 1.383(3) . ?
C17 C18 1.377(3) . ?
C17 C22 1.403(3) . ?
C11 C12 1.518(3) . ?
C22 C21 1.384(3) . ?
C13 C14 1.523(3) . ?
C13 C12 1.523(3) . ?
C18 C19 1.386(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.396(3) . ?
C23 C24 1.540(3) . ?
C15 C14 1.512(3) . ?
C10 C9 1.520(3) . ?
C9 C8 1.521(3) . ?
C19 C20 1.382(3) . ?
C6 C5 1.371(3) . ?
C21 C20 1.390(3) . ?
C2 C3 1.385(4) . ?
C5 C4 1.388(3) . ?
C3 C4 1.379(4) . ?
